JPH06211785A - Substituted 2-arylpyrrole - Google Patents

Abstract

PURPOSE: To provide the new arylpyrrole compounds which have low toxicity and are excellent in molluscicidal activity, bactericidal/fungicidal activity and insecticidal activity and therefore, useful as pesticides or the like.

CONSTITUTION: The arylpyrrole compounds are those represented by the formula I [wherein: each of R¹ and R² is H or a halogen; R³ is H, a halogen or a (substituted) alkyl group; R⁴ is H or a group represented by the formula II (R⁵ is H or an alkyl group; and R⁶ is H, an alkyl group, or the like); Ar is a (substituted) aryl group; each of X¹ and X² is H or a halogen; and (n) is an integer of 0 to 2], such as 2-(4-chlorophenyl)-3- bromo-5-(trifluoromethylsulfonyl)-pyrrole. Such a compound represented by the formula I is prepared, for example, by reacting a compound represented by the formula III ((n) is 1 or 2) with a halogenating agent.

COPYRIGHT: (C)1994,JPO

Description

Detailed Description of the Invention

The present invention relates to novel substituted 2-arylpyrroles, a process for their preparation and novel intermediates for their preparation, and their pests, in particular agriculture, forestry, the protection of stored substances and materials, and the field of hygiene. It relates to the use for controlling harmful insects, mites and nematodes encountered.

It has already been shown that structurally similar cyanopyrroles have molluscicidal, fungicidal and insecticidal activity [European patent (EP-A)].
0,347,488, European patent (EP-A) 0,358,047, European patent (EP-A) 0,312,723, German published patent (DE-A) 4, 117,752, European Patent (EP-A) 0,481,182, European Patent (EP-A) 0,484,614]. However, the activity and the range of action of these compounds are not always completely satisfactory, especially when the amount used is low and the concentration used is low.

Now, the general formula (I)

[0004]

[Chemical 14]

In the formula, R ¹ and R ² independently represent hydrogen or halogen. However, at least one of the two radicals R ¹ or R ² represents halogen, R ³ represents hydrogen, halogen or optionally substituted alkyl, Wherein R ⁵ represents hydrogen, or optionally substituted alkyl, and R ⁶ is hydrogen, optionally substituted alkyl or Wherein R ⁷ and R ⁸ independently of one another represent hydrogen, alkyl, alkenyl, alkynyl, alkoxycarbonyl, alkenoxycarbonyl, alkynoxycarbonyl or acyl, and R ⁷ and R ⁸ are bound to them. It is also possible to form a ring with N atom, Ar
Substituted 2-arylpyrroles have been discovered in which represents optionally substituted aryl, X ¹ and X ² independently of one another represent hydrogen or halogen, and n represents 0, 1 or 2.

Furthermore, in each case the substitution 2-of the formula (I)
Arylpyrroles can be prepared according to the kind of their substituents by suitable synthetic steps, while at the same time one group of final products of formula (I) is prepared for another group of final products of formula (I). It has been discovered that it can be an intermediate of. The outline thereof is shown in reaction formula 1.

[0007]

[Chemical 15]

For example, the formula (Ia)

[0009]

[Chemical 16]

Wherein R ¹ , R ² , R ³ , X ¹ , X ² and Ar
Has the meanings given above, and n is 1 or 2, a substituted 2-arylpyrrole of A is of the formula (II)

[0011]

[Chemical 17]

A 2-arylpyrrole, wherein R ³ , X ¹ , X ² and Ar have the meanings given above and n is 1 or 2, is reacted with a halogenating agent (method A). Or B) Formula (III)

[0013]

[Chemical 18]

Wherein R ¹ , R ² , R ³ , X ¹ , X ² and Ar
A has a meaning as described above, is obtained by reacting a 2-arylpyrrole with an oxidizing agent (method B) or C) a compound of formula (Ib)

[0015]

[Chemical 19]

Wherein R ¹ , R ² , R ³ , X ¹ , X ² and Ar
Has the meanings given above, and n is 1 or 2, and Is a 2-arylpyrrole of the formula (Ia) in which R ¹ , R ² , R ³ , X ¹ , X ² and Ar have the meanings given above and n is 1 or The 2-arylpyrrole which is 2 has the formula (IV)

[0017]

Embedded image R ⁹ —X ³ (IV) wherein R ⁹ has the meanings given above and X ³ represents an anionic residual group, and, if appropriate, in the presence of a base, And / or if appropriate can be obtained by reacting in the presence of a diluent (method C), or D) of formula (Ic)

[0018]

[Chemical 21]

Wherein R ¹ , R ² , R ³ , X ¹ , X ² and Ar
Has the meaning given above, 2-Arylpyrrole wherein R ⁵ and R ⁶ have the meanings given above, and n is 1 or 2, and are further represented by the general formula (III), in which R ¹ , R ² , R ³ , X ¹ ,
A ^2- arylpyrrole, in which X ² and Ar have the meanings given above, can be prepared according to

[0020]

Embedded image R ⁹ —X ³ (IV) wherein R ⁹ has the meanings given above and X ³ represents an anion residue, and, if appropriate, in the presence of a base, and And / or, if appropriate, can be obtained by reacting in the presence of a diluent (method D) or E) of formula (Id)

[0021]

[Chemical formula 23]

Wherein R ¹ , R ² , R ³ , X ¹ , X ² and Ar
Has the meaning given above, and n is 0, 2-
The arylpyrrole is further represented by the formula (V)

[0023]

[Chemical formula 24]

2-arylpyrroles of the formula where R ³ , X ¹ , X ² and Ar have the meanings given above are obtained by reaction with a halogenating agent (method E).

(The substituted 2-arylpyrroles of general formula (Id) are identical to the precursors described as general formula (III).) Finally, the novel substituted 2-arylpyrroles of formula (I) are With its outstanding biological activity, it is particularly suitable for the protection of agricultural, forestry, stored products and materials, and pests encountered in the field of hygiene, especially insects, mites and nematodes. The novel substituted 2-arylpyrroles of the formula (I) are furthermore suitable for controlling fungi and fungi which cause plant disease.

Preferred substituted 2-arylpyrroles of the above formula (I) are those in which R ¹ and R ² independently of one another represent hydrogen, bromine or chlorine, at least one of the radicals R ¹ or R ² being bromine or chlorine. And R ³ is hydrogen, fluorine, chlorine, bromine, or (optionally 1 to 5 fluorine, chlorine,
Or optionally substituted by the same or different substituents selected from the group consisting of bromine atoms) C ₁ -C _5-
Represents alkyl, Wherein R ⁵ is hydrogen, or (optionally by 1 to 5 identical or different halogen atoms, C ₁ -C ₅ -alkoxy, C ₁ -C ₅ -alkylthio, C ₁ -C ₅ -acyloxy, C ₂ — C _6- Alkoxycarbonyl, phenyl, cyano, or nitro) C _1-
Represents C ₅ -alkyl and R ⁶ is hydrogen or (optionally by 1 to 5 identical or different halogen atoms, C ₁ -C ₈ -alkoxy, C ₁ -C ₈ -alkylthio,
C ₁ -C ₆ -acyloxy, C ₂ -C ₈ -alkoxycarbonyl, phenyl, cyano or nitro) C ₁ -C ₆ -alkyl, or Wherein R ⁷ and R ⁸ independently of one another are hydrogen, C ₁ -C ₈ -alkyl, C ₃ -C ₈ -alkenyl, or C ₃ -C ₈ -alkynyl (wherein the alkyl, alkenyl and alkynyl are each optionally 1 to 6 identical or different halogen atoms, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -alkylthio, C ₁ -C ₆ -acyloxy, (C ₁ -C ₆ -alkoxy) -carbonyl, optionally substituted Optionally substituted by phenyl, cyano, or nitro), or (C ₁ -C ₈ -alkoxy) -carbonyl,
(C ₃ -C ₈ -Alkenoxy) carbonyl, or (C ₃
-C ₈ -alkynoxy) -carbonyl, (the same alkoxy, alkenoxy and alkynoxy groups are each optionally 1 to 6 identical or different halogen atoms, C
₁ -C ₆ - alkoxy, C ₁ -C ₆ - alkylthio, C ₁ -
C ₆ -acyloxy, (C ₁ -C ₆ -alkoxy) -carbonyl, optionally substituted and optionally substituted by phenyl, cyano, or nitro) or C ₁ -C ₈ -acyl (acyl Is optionally ₁ to 6 identical or different halogen atoms, C ₁ -C ₆ -alkoxy,
C ₁ -C ₆ -alkylthio, C ₁ -C ₆ -acyloxy,
(C ₁ -C ₆ -alkoxy) -carbonyl, optionally substituted phenyl, cyano, or nitro), or R ⁷ and R ⁸
Together with the N atom to which they are attached form a 4- to 8-membered ring, and Ar is optionally halogen, C _1-.
C ₈ - alkyl, C ₂ -C ₈ - alkenyl or C ₂ -C,
₈ -alkynyl (wherein the alkyl, alkenyl and alkynyl are each optionally ₁ to 6 identical or different halogen atoms, C ₁ -C ₅ -alkoxy, C ₁ -C ₅ -alkylthio, C ₁ -C ₅ -acyloxy, And an alkoxy and an alkylthio group each may be substituted by 1 to 6 halogen atoms) C ₁ -C ₈ -alkoxy, C ₂ -C ₈ -alkenoxy, or C ₂ -C ₈ -alkynoxy (the same alkoxy, Alkenoxy and alkynoxy can each optionally be substituted by 1 to 6 identical or different halogen atoms) C ₁
-C ₈ - substituted by alkynylthio (the alkylthio, alkenylthio and alkynylthio, respectively, to 1 at any time six identical or different halogen atoms - alkylthio, C ₂ -C ₈ - alkenylthio or C ₂ -C _8, C ₂ -C ₈ -acyloxy (wherein the acyloxy may be optionally substituted by 1 to 6 halogen atoms), amino (wherein the amino is optionally 1 to 2 identical or different, 1 to The same or different substituents from the group consisting of alkyl groups having 8 carbon atoms and, if appropriate, 1 to 6 halogen atoms, or halogenoalkyl groups), nitro or cyano. Represents phenyl, which may be mono- or pentasubstituted, and is represented by X ¹ and X ² Are each independently hydrogen, fluorine, chlorine or bromine, and n is 0, 1, or 2;
It is an arylpyrrole.

Particularly preferred substituted 2-arylpyrroles of the formula (I) are those in which R ¹ and R ² independently of one another represent hydrogen, bromine or chlorine, at least one of the radicals R ¹ or R ² being bromine or chlorine. R ³ is hydrogen, fluorine, chlorine, bromine, or (optionally 1 to 5 fluorine, chlorine,
Or it may be substituted by identical or different substituents selected from the herd consisting of bromine) C ₁ -C ₄ -
Represents alkyl, Wherein R ⁵ is hydrogen, or (optionally by 1 to 5 identical or different halogen atoms, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -alkylthio, C ₁ -C ₄ -acyloxy, C ₂ — C ₅ -Alkoxycarbonyl, optionally substituted by phenyl, cyano, or nitro) C _1-
Represents C ₄ -alkyl and R ⁶ is hydrogen or (optionally by 1 to 5 identical or different halogen atoms, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -alkylthio,
C ₁ -C ₅ -acyloxy, C ₂ -C ₆ -alkoxycarbonyl, phenyl, cyano, or nitro) C ₁ -C ₅ -alkyl, or In the formula, R ⁷ and R ⁸ are each independently hydrogen, C ₁ -C ₆ -alkyl, C ₃ -C ₆ -alkenyl, or C ₃ -C ₆ -alkynyl (wherein the alkyl, alkenyl and alkynyl are each independently 1 to 5 identical or different fluorine and / or chlorine atoms, C ₁ -C ₄ -alkoxy, C _1-
C ₄ - alkylthio, C ₁ -C ₄ - acyloxy, (C ₁ -
C ₄ -alkoxy) -carbonyl, optionally substituted phenyl, cyano, or optionally substituted by nitro), or (C ₁ -C ₆ -alkoxy) -carbonyl, (C ₃ -C ₆ -Alkenoxy) carbonyl, or (C ₃ -C ₆ -alkynoxy) -carbonyl, (the same alkoxy, alkenoxy and alquinoxy are each optionally 1 to 5 identical or different fluorine and / or chlorine atoms, C ₁ -C ₄ -Alkoxy,
C ₁ -C ₄ -alkylthio, C ₁ -C ₄ -acyloxy,
Represents (C ₁ -C ₄ -alkoxy) -carbonyl, optionally substituted by phenyl, cyano, or nitro), or C ₁ -C ₆ -acyl (wherein the acyl is optionally from 1 to 5). Identical or different fluorine and / or chlorine atoms, C ₁ -C ₄ -alkoxy, C ₁
-C ₄ - alkylthio, C ₁ -C ₄ - acyloxy, (C ₁
-C ₄ -alkoxy) -carbonyl, optionally substituted phenyl, cyano, or nitro) or R ⁷ and R ⁸ are the same as the N atom to which they are attached. Together, they form a 4- to 8-membered ring, wherein Ar is optionally fluorine, chlorine, or bromine, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, or C _2-. C ₆ -alkynyl (wherein the alkyl, alkenyl and alkynyl are each independently 5 fluorine and / or chlorine atoms, _{1 to 4} C-alkoxy, C ₁ -C ₄ -alkylthio, C ₁ -C ₄ -acyloxy) And here the alkoxy, alkylthio groups can each be substituted by 1 to 5 fluorine and / or chlorine atoms) C ₁ -C ₆ -alkoxy,
C ₂ -C ₆ -Alkenoxy, or C ₂ -C ₆ -alkynoxy (wherein the alkoxy, alkenoxy and alkynoxy may each optionally be substituted by 1 to 5 fluorine and / or chlorine atoms) C ₁ -C ₆ - alkylthio, C ₂ -C ₆ - alkenylthio or C ₂ -C _6, -
Alkynylthio (the alkylthio, alkenylthio and alkynylthio may each optionally be substituted by 1 to 5 fluorine and / or chlorine atoms) C ₂ -C ₆ -acyloxy (the acyloxy being optionally 1
To optionally 5 halogen atoms), amino (wherein the amino is optionally 1 to 2 identical or different 1 to 6 carbon atoms and, if appropriate, 1 to 5 fluorine and Or optionally substituted by an alkyl group having a chlorine atom), nitro or cyano, and phenyl, which may optionally be mono- or tetra-substituted by the same or different substituents from the group consisting of X ¹ and X ² each independently represent hydrogen, fluorine or chlorine, and n is 0,
It is a 2-arylpyrrole representing 1 or 2.

The general and preferred radical definitions and explanations given above apply to the end products and also to the starting materials and intermediates. The definitions of these radicals can, if desired, also be combined with one another, ie between the particularly preferred meanings.

If, according to Preparation Method A, 2- (4-chlorophenyl) -5- (trifluoromethylsulfonyl)
-If pyrrole and bromine are used as starting materials,
The reaction process can be expressed by the following equation.

[0030]

[Chemical 25]

If, according to Process B, 2- (4-chlorophenyl) -3,4-dibromo-5- (trifluoromethylthio) -pyrrole and m-chloro-perbenzoic acid are used as starting materials The reaction process can be expressed by the following equation.

[0032]

[Chemical formula 26]

If production method C is used, 2- (3,4-
If dichlorophenyl) -3-bromo-5- (chlorodifluoromethylsulfonyl) -pyrrole and chloromethyl ethyl ether are used as starting materials, the reaction process can be represented by the following equation.

[0034]

[Chemical 27]

If, according to Process D, 2- (4-chlorophenyl) -3,4-dibromo-5- (chlorodifluoromethylthio) -pyrrole and chloromethylethyl ether are used as starting materials, the reaction process Can be expressed by the following equation.

[0036]

[Chemical 28]

If, according to the manufacturing method E, 2- (4-chlorophenyl) -5- (chlorodifluoromethylthio)-
If pyrrole and bromine are used as starting materials, the reaction process can be represented by the following equation.

[0038]

[Chemical 29]

Process for making compounds of formula (Ia)
A is characterized by treating a 2-arylpyrrole of formula (II) with a halogenating agent.

Diluents which can be used in method A are all customary solvents. Hydrocarbons such as benzene and hexane, halogenated hydrocarbons such as chloroform and methylene chloride, as well as ethers such as dibutyl ether, tetrahydrofuran, dioxane, and organic acids such as formic acid and acetic acid are preferably used. Water can also be used as a diluent.

Halogenating agents which can be used are all customary halogenating agents. Preferably, chlorine, bromine, sodium hypochlorite, potassium hypochlorite, sodium hypobromite, potassium hypobromite, sulfuryl chloride, t-butyl hypochlorite, N-chlorosuccinimide, and N-
Bromosuccinimide is used.

The reaction temperature can be varied within a considerable range. Generally, the process is carried out at temperatures between -10 ° C and + 120 ° C, preferably 0 ° C to 70 ° C.

When carrying out the process, the reaction components of the formula (II) are reacted with equimolar or excess amounts of halogenating agent.

The reaction is generally carried out under atmospheric pressure.
When using chlorine and bromine, the reaction is carried out under pressure (5.0
00 hPa or less).

Process for preparing compounds of formula (Ia)
B is characterized by reacting the 2-arylpyrrole of formula (III) with an oxidizing agent.

Diluents which can be used in Method B are all customary solvents. Hydrocarbons such as benzene and hexane, halogenated hydrocarbons such as chloroform and methylene chloride, as well as ethers such as dibutyl ether, tetrahydrofuran, dioxane, and organic acids such as formic acid and acetic acid are preferably used. Water can also be used as a diluent.

The oxidizing agents which can be used are all customary oxidizing agents. Preferably m-chloroperbenzoic acid, sodium peroxide pyrosulfate (oxone), magnesium monoperoxyphthalate, hydrogen peroxide, atmospheric oxygen in the presence of a catalyst,
Potassium permanganate or CrO ₃ is used.

The reaction temperature can be varied within a considerable range. Generally, the process is carried out at a temperature of -30 ° C to + 200 ° C, preferably -10 ° C to + 80 ° C.

In carrying out the process, the reaction components of the formula (III) are reacted with 1 or 2 equivalents of oxidizing agent, depending on the desired degree of oxidation of sulfur. If appropriate, it is also possible to use excess oxidizing agent.

Process for preparing compounds of formula (Ib)
C is a 2-arylpyrrole of formula (Ia) represented by formula (IV)
Is characterized by reacting with a compound of (I) in the presence of a base, if appropriate, and in the presence of a diluent, if appropriate.

The diluents which can be used in Method C are all customary inert organic solvents. Preferably, hydrocarbons such as benzene, toluene, xylene, as well as ethers such as dibutyl ether, tert.-butyl methyl ether, tetrahydrofuran, dioxane, and polar solvents,
Examples include dimethyl sulfoxide, acetonitrile, sulfolane, dimethylformamide and N-methyl-pyrrolidone.

Bases which can be used are all customary proton acceptors. Preferably alkali metal oxides, alkali metal hydroxides, alkali metal carbonates, alkaline earth metal oxides, alkaline earth metal hydroxides, alkaline earth metal carbonates such as sodium hydroxide, potassium hydroxide, oxidation Included are magnesium, calcium oxide, sodium carbonate, potassium carbonate, and calcium carbonate, all of which are also used in the presence of intercalation catalysts such as triethylbenzylammonium chloride, tetrabutylammonium bromide, or 18-crown-6. it can. Alkali metal amides, alkali metal hydrides, alkaline earth metal amides, and alkaline earth metal hydrides such as sodium amide, sodium hydride, and calcium hydride, and also alkali metal alcoholates such as sodium methylate, sodium ethylate. , And potassium tert.-butyrate can also be used.

When carrying out the process, the reaction temperatures can be varied within a considerable range. Generally, the method is -10 ° C.
To 200 ° C, preferably 0 ° C to 120 ° C.

When carrying out the process, the reaction components of the formula (Ia), the deprotonating base and the components of the formula (IV) are generally used in approximately equimolar amounts. However, one component or the other two components may be used in a large excess (3 mol or less).

Method C is generally carried out at atmospheric pressure. However, it is also possible to carry out under a pressure higher than atmospheric pressure.

Process for preparing compounds of formula (Ic)
D is a 2-arylpyrrole of formula (III) represented by formula (I
It is characterized by reacting a compound of V) with a base, if appropriate, and in the presence of a diluent, if appropriate.

Suitable diluents for Method D are all customary inert organic solvents. Preferably hydrocarbons such as benzene, toluene, xylene as well as ethers such as dibutyl ether, tert.-butyl methyl ether,
Tetrahydrofuran, dioxane, as well as polar solvents such as dimethyl sulfoxide, acetonitrile, sulfolane, dimethylformamide and N-methyl-pyrrolidone are mentioned.

Bases which can be used are all customary proton acceptors. Preferably alkali metal oxides, alkali metal hydroxides, alkali metal carbonates, alkaline earth metal oxides, alkaline earth metal hydroxides, alkaline earth metal carbonates such as sodium hydroxide, potassium hydroxide, oxidation Included are magnesium, calcium oxide, sodium carbonate, potassium carbonate, and calcium carbonate, all of which are also used in the presence of intercalation catalysts such as triethylbenzylammonium chloride, tetrabutylammonium bromide, or 18-crown-6. it can. Alkali metal amides, alkali metal hydrides, alkaline earth metal amides, and alkaline earth metal hydrides such as sodium amide, sodium hydride, and calcium hydride, and also alkali metal alcoholates such as sodium methylate, sodium ethylate. , And potassium tert.-butyrate can also be used.

When carrying out the process, the reaction temperatures can be varied within a considerable range. Generally, the method is -10 ° C.
To 200 ° C, preferably 0 ° C to 120 ° C.

In carrying out the process, the reaction components of formula (III), the deprotonating base and the components of formula (IV) are generally used in approximately equimolar amounts. However, it is also possible to use one component or the other two components in a large excess (3 mol or less).

The method is generally carried out under atmospheric pressure. However, it is also possible to carry out under pressure.

Process E for preparing the compounds of formula (Id) (= III) is characterized by treating the 2-arylpyrrole of formula (V) with a halogenating agent.

The diluents which can be used in Method E are all customary solvents. Hydrocarbons such as benzene and hexane, halogenated hydrocarbons such as chloroform and methylene chloride, as well as ethers such as dibutyl ether, tetrahydrofuran, dioxane, and organic acids such as formic acid and acetic acid are preferably used. Water can also be used as a diluent.

Halogenating agents which can be used are all customary halogenating agents. Preferably chlorine, bromine, sodium hypochlorite, potassium hypochlorite, sodium hypobromite, potassium hypobromite, sulfuryl chloride, t-butyl hypochlorite, N-chlorosuccinimide, and N-bromo. Succinimide is used.

The reaction temperature can be varied within a considerable range. Generally, the process is carried out at temperatures between -10 ° C and + 120 ° C, preferably 0 ° C to 70 ° C.

In carrying out the process, the reaction components of the formula (V) are reacted with equimolar or excess amounts of halogenating agent.

The reaction is generally carried out at atmospheric pressure.
When using chlorine and bromine, the reaction is carried out under pressure (5.0
00 hPa or less).

The starting materials of the general formula (II) necessary for preparing the compounds of the general formula (Ia) by method A are new. The compound has the formula (V)

[0069]

[Chemical 30]

Wherein R ³ , X ¹ , X ² and Ar have the meanings given above and are obtained by reacting a 2-arylpyrrole with an oxidizing agent.

If, for example, 2- (4-chlorophenyl)
-5- (chlorodifluoromethylthio) -pyrrole and m
If -chloro-perbenzoic acid is used as a starting material, the reaction process of the production method can be represented by the following equation.

[0072]

[Chemical 31]

The present process for preparing compounds of formula (II) is characterized by reacting a 2-arylpyrrole of general formula (V) with an oxidizing agent.

Diluents which can be used in this way are all customary solvents. Hydrocarbons such as benzene and hexane, halogenated hydrocarbons such as chloroform and methylene chloride, as well as ethers such as dibutyl ether, tetrahydrofuran, dioxane, and organic acids such as formic acid and acetic acid are preferably used. Water can also be used as a diluent.

The oxidizing agents which can be used are all customary oxidizing agents. Preference is given to using m-chloroperbenzoic acid, potassium hydrogen pyrosulfate (oxone), magnesium monoperoxyphthalate, hydrogen peroxide, atmospheric oxygen in the presence of a catalyst, potassium permanganate or CrO ₃ .

The reaction temperature can be varied within a considerable range. Generally, the process is carried out at a temperature of -30 ° C to + 200 ° C, preferably -10 ° C to + 80 ° C.

In carrying out the process, the reaction components of formula (V) are reacted with 1 or 2 equivalents of oxidizing agent, depending on the desired degree of oxidation of sulfur. If appropriate, it is also possible to use excess oxidizing agent.

The starting materials of the formula (V) are new. The substance has the general formula (VI)

[0079]

[Chemical 32]

Wherein Ar has the meaning given above, 2
-Arylpyrrole having the general formula (VII)

[0081]

[Chemical 33] In the presence of sulphenyl chloride, wherein X ¹ , X ² and R ³ have the meanings given above, and, if appropriate, a base,
And, if appropriate, obtained by reacting in the presence of a diluent.

According to this production method, 2- (3,4-
If dichlorophenyl) -pyrrole and trifluoromethylsulfenyl chloride are used as starting materials, the reaction process can be represented by the following equation:

[0083]

[Chemical 34]

The present process for the preparation of compounds of formula (V) comprises the preparation of 2-arylpyrroles of formula (VI) with the general formula (VI)
It is characterized by reacting a compound of I) in the presence of a base, if appropriate, and in the presence of a diluent, if appropriate.

Suitable diluents for the process are all customary inert organic solvents. Preferably hydrocarbons such as benzene, toluene, xylene as well as ethers such as dibutyl ether, tert.-butyl methyl ether,
Tetrahydrofuran, dioxane, as well as polar solvents such as dimethyl sulfoxide, acetonitrile, sulfolane, dimethylformamide and N-methyl-pyrrolidone are mentioned.

Bases which can be used are, for example, alkali metal amides, alkali metal hydrides, alkaline earth metal amides and alkaline earth metal hydrides such as sodium amide, sodium hydride and calcium hydride, and also alkali Metal alcoholates such as sodium methylate, sodium ethylate, and potassium tert.-butyrate.

When carrying out the process, the reaction temperatures can be varied within a considerable range. Generally, the method is -70 ° C.
To + 50 ° C., preferably −30 ° C. to + 30 ° C.

When carrying out the process, the components of the formulas (VI) and (VII) are generally used in approximately equimolar proportions. If appropriate, it is also possible to use the reaction components of the formula (VII) in excess.

The bases which can be used are generally used in equimolar amounts or in slight excess.

The method is generally carried out under atmospheric pressure. If gaseous sulphenyl chloride is used, it is also possible to carry out the reaction under pressure (up to 5,000 hPa).

The 2-arylpyrroles of general formula (VI) are known and can be prepared by known methods [A. Go
Ssauer, Die Chemie der Py
rrole (chemistry of pyrrole) Springer-Ve
rlag (Berlin), 1974, 276
Page; Engel, W.M. Steglich, Ange
w. See Chemie 90 , 719 (1978)].

Some of the sulfenyl chlorides of the general formula (VII) are known and can be prepared in principle by known methods (Houben-Weyl, Georg T.
hieme-Verlag Stuttgart, Vo
l. 9, p. From 267 onward, German published patent No. 4,
036,515).

The 2-arylpyrroles of the formula (I) according to the invention are useful for the protection of pests, in particular for the protection of agriculture, forestry, stored products and materials, and the control of insects, nematodes and mites encountered in the field of hygiene. , And is well tolerated by plants, and its toxicity to warm-blooded animals is also preferably low. These 2-arylpyrroles are active against both non-resistant and resistant species and at all stages of growth and development, or against individual stages thereof.

The pests mentioned above include the following:

Isopoda, for example, Oniscus asellus, cadaver beetle (Armadillidium vulg)
are) and woodlouse (Porcellio sc)
abar), Chilopoda, for example, Geophilus carpophagu
s) and motogeji species (Scutigera sp.
p. ), Symphyla, for example, Scutigellaella im
maculata (companion of Komukade), Thyme (Th
ysanura), for example Western spots (Lepisma)
saccharina), Collembola (Collemb)
ola), for example, Onychiuruu
s armatus), Orthopteran (Orthopter)
a), for example, Blattaorie
ntalis), American cockroach (Periplane)
ta americana), Leucophaea maderae, German cockroach (Blattela germanica),
Acheta domestics
icus), Kera (Grillottalpa sp.
p. ), Tonosama grasshopper (Locusta migra)
toria migratrioides, Melanoplus
differentialis), and cystocerca
Gregaria (Schistocerca gregar)
ia), the earwig (Dermaptera), for example, the earwig Beetle (Forficula auri)
Clararia), Termites (Isoptera),
For example, Reticuliterm
es spp. ), Anoplura, for example, aphids (Phylloxeravastat)
Rix), Penfigus (Pemphigus sp)
p. ) And human lice (Pediculus huma)
nus corporis), bedbug (Haem)
atopinus spp. ), And Lithognathus spp. (Lalognathus spp.), For example, Malophaga, Trichodectes spp. And Damalinea spp.
alis) and Negia thrips (Trips tab)
aci), Hemiptera (Heteroptera), for example the white stink bug (Eurygaster sp)
p. ), The stink bug (Dysdercus inte)
rmedius), Piesma quadrata (Piesm)
a quadrata), Bedbug (Cimex)
Lectula aria), Common tortoise (Rhodniu)
sprlixus) and leatherback turtle (Triato)
ma spp. ), Homoptera, for example, Aleurodes brassicae (Aleurodes)
brassicae), cotton whitefly (Bemisi)
a tabaci), Trialeurodes vapororiorum
um), Aphis gossypii
i), Japanese radish aphid (Brebiocoryne)
brassase), Cryptomyzus ribis, Doloris
Pomi (Doralis pomi), Apple Beetle (Eriosoma lanigerum), Peach Aphid (Hyalopterus arundi)
nis), Aphis gossypii (Macrosip)
hum avenae), Aphid (Myzus)
spp. ), Hot Aphid (Phorodon)
humuli), wheat aphid (Rhopa)
losiphum padi), leafhopper (Emp)
oasca spp. ), Euscelis bilobatus, Nephotettix cinchtice
ps), Cornus scales (Lecanium)
corni), olive scale insect (Saiss)
etia oleae), Hitobibunka (Laode)
lphax striatellus), brown planthopper (Nilaparvata striatellu)
s), Red scale bug (Aonidiella)
aurantii), white scale bug (Aspi)
diotus hederae, Pseudococcus spp., and Psylla spp., Lepidoptera (Lepido)
ptera), such as the cotton bollworm (Pectino)
phora gossypiella), Bupalus piniarus,
Cheymatobia b
rumata), Rhizocorretis blanccaldera (Li
thocollettis blankardell
a), Hyponomeuta Padera
a padella), diamondback moth (Plutella m)
aculipennis), Japanese plum bug (Malaco)
soma neustraia, crocodile beetle (E
upchris chrysorrhea, Lymantria spp., Bucculartrix t
harberiella), mandarin orange moth (Phy)
llocnistis citrella), Yaga (A
grotis spp. ), Euxoa
spp. ), Feltia spp.,
Aerias insulana
na), Heliothis sp
p. ), Spodoptera litura (Laphygma exi)
gua), weevil (Mamestra brass)
icae), Panoris flaméa (Panolis f)
lammea), Hasmonyoto (Prodenia)
litura), Shirona yoto (Spodoptera)
spp. ), Trichoplasia Ni (Trichopl)
usia ni), Carpocapsa Pomonella (Carp)
occapsa pomonella), caterpillar (Pi)
eris spp. ), Nikameichu (Chilo
spp. ), Awanomeiga (Pyrausta nub)
ilalis), Japanese cod moth (Ephest)
ia kuehniella), Honey hemlock (Gall)
eria melonella), Tineola bisselliella,
Tinea pellinone
lla), Hoffmanofila Pseudosprestella (H
ofmannofila pseudoseprete
lla), Cacoecia podana (Cacoecia p
Odana), Capua rechiclana
ticulana), Choristoneura fumiferana
a), Clysia Ambue
ituella), Chahamaki (Homona mag)
nima), and Tortoliskus biridana (To
rtrix viridana), Coleoptera (Coleo)
ptera), for example, Anovium punctatum (An
ovium punctatum), Rhizopertha dominica,
Burkidus of Tectos
ectus), Bean weevil (Acantho)
scelodesobectus), hirotorupesu ・
Hylotrupes bajulu
s), Agelastica Arni (Agelastica)
alni), Leptino Tulsa desemlineta (Lep
Tinotarsa decinedata), mustard beetle (Phaedon cochlearia)
e), Diabrotica sp
p. ), Psyliodes Chrysocephala (Psylli)
odes chrysocepalla, Epilachna varives
tis), Atomaria sp
p. ), A saw beetle (Oryzaephilu)
s surinamensis), weevil (An)
thonomus spp. ), Weevil (Sit
opilius spp. ), Otiorrhynchus sulcatu
s), weevil (Cosmopolites)
sordidus), Shoot-Lynchus assimili
s), Hypera postica
a), Dermestes sp
p. ), Trogoderma sp
p. ), Anthrenus sp
p. ), Attagenus sp.
p. ), Flatworm Beetle (Lyctus sp)
p. ), Meligetes Aeneus
s aeneus), leopard beetle (Ptinus)
spp. ), Niptus
holleucus), Selma leopard beetle (Gi
bbium psylloides), Trifolium spp., Tenemrio molito
r), click beetles (Agriotes spp.),
Conoderus spp., Melolontha melolosa
ontha), Amfimaron Solstica squirrel (A
mphimallon solstitialis),
And Costelitra zealandika
a zealandica), Hymenoptera (Hymenop)
tera), for example pine bee (Diprion sp)
p. ), Hoplocampa sp
p. ), Lasius spp., Monomorium pharaonis
And hornets (Vespa spp.), Diptera (D)
iptera), for example, Aedes sp.
p. ), Anopheles sp. (Anopheles sp
p. ), Culex spp., Drosophila melanog
aster, Musca spp., Fannie spp., Calliphory erythro.
cephala), fruit fly (Lucilia sp.
p. ), Chrysomya sp.
p. ), Cuterebra sp
p. ), Horsefly (Gastrophilus sp.
p. ), The fruit fly (Hyppobosca sp)
p. ), Sand flies (Stomoxys spp.), Sheep flies (Oestrus spp.), Bull flies (H)
ypoderma spp. ), Abu (Tabanus)
spp. ), Tania (Tannia spp.), Mosquito flies (Biobio hortulanus), Oscinella frito, Phorbia spp.
tata), fruit fly oleae (Dacus olea)
e) and Gumambo Paldosa (Tipula pal)
udosa), fleas (Siphonaptera),
For example, Keopsunezumimi (Xenopsylla c
heopis), and Naganomi (Ceratopyl)
usspp. ), Arachnida, eg, Scorpio maurus
s) and Latrodectus Mactans (Latrod)
ectus mactans, Acarinidae (Acarin)
a), for example, Acarus sir
o), a house dust mite (Argas spp.), a woodpecker mite (Ornithodoros spp.), and a black spider (D)
ermanyssus galllinae, Eriophyes ribi
s), citrus rust mite (Phyllocoptruta)
oleivora), Bovine
us spp. ), Koi tick (Rhipiceph)
alus spp. ), Amblyom
ma spp. ), The tick, Hyalomma s
pp. ), Ticks (Ixodes spp.), Dermatophagoides chinensis (Psooptes spp.)
p. ), Harbor mite (Sarcoptes sp)
p. ), Dust (Tarsonemus sp)
p. ), Clover spider mites (Bryobia praeti)
osa), mandarin orange spider mite (Paonychus)
spp. ), And the spider mite (Tetranychu)
s spp. ), The substituted 2-arylpyrroles of the formula (I) according to the invention are not only active against plant, hygiene and storage product tests, but also in the veterinary field as animal parasites [ectoparasites]. For example, it is also active against scale ticks, scab ticks, house dust mites, mites, flies (stabs, sucks blood, etc.), parasite larvae of flies, lice, lice, lice, flea. The compounds are active against normal non-resistant and resistant species and strains, as well as all parasitic and non-parasitic stages of ectoparasite development.

The substituted 2-arylpyrroles of the formula (I) of the present invention show high insecticidal activity not found in other compounds. The active compound is an insect which is harmful to plants, for example, Phaedon cochlear larvae.
iae), green peach aphid (Myzus pers)
icae) or black aphid (Aphisf)
It can be used particularly effectively for abae). In the present invention, the active compound exhibits not only a protective action but also a systemic action via leaves and roots.

Furthermore, the substituted 2-arylpyrroles of the formula (I) according to the invention are also suitable for controlling soil insects, for example onion maggots (Phorbia antiq) in soil.
It can be used for controlling ua).

Furthermore, the substituted 2-arylpyrroles of the formula (I) according to the invention have a strong action against hygiene pests and storage substance pests, for example the German cockroach (Blattell).
agermanica).

Finally, the novel active compounds of the formula (I) are also suitable for controlling fungi which cause plant diseases, for example the active compounds, for example rice blast (Py).
ricularia oryzae).

The active compounds are incorporated into customary formulations, for example solutions, emulsions, dispersants, powders, foams, coatings, granules, aerosols, natural and synthetic materials impregnated with active compounds, polymeric substances. Ultrafine particle capsules for dispersion or seed coating, further fumigation equipment, such as fumigation cartridges,
Compounds used in fumigation cans, fumigation coils, and ULV
It can be a mix for cold and warm mists.

These formulations are prepared in a known manner, for example by adding the 2-arylpyrroles of the formula (I) according to the invention as extenders, ie liquid solvents, liquefied gas under pressure, and / or solid carriers, and optionally surfactants, That is, it is manufactured by mixing using an emulsifier and / or a dispersant and / or a foaming agent. When water is used as extender, organic solvents, for example, can also be used as cosolvents.

Suitable, but predominant, liquid solvents are aromatic compounds such as xylene, toluene, alkylnaphthalenes, chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlorobenzene, chloroethylene or chlorinated compounds. Methylene, aliphatic hydrocarbons such as cyclohexane, or paraffins such as mineral oil fractions, alcohols such as butanol or glycols and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, highly polar. Solvents such as dimethylformamide and dimethylsulfoxide, and water.

The liquefied gas extender or carrier means a liquid which is gaseous at room temperature and atmospheric pressure, for example, an aerosol propellant, and examples thereof include halogenated hydrocarbon and butane, propane, nitrogen and carbon dioxide.

Suitable as solid carriers are, for example, ground natural minerals such as kaolin, clay, talc,
There are chalk, quartz, attabalgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as highly disperse silicic acid, alumina and silicates.

Suitable as solid carriers for granules are:
For example, ground and classified natural rocks such as limestone, marble, pumice, sepiolite and dolomite and artificial granules of inorganic and organic groats, and organic granules such as sawdust, coconut shells, corn cobs and tobacco stems. There is.

Suitable as emulsifiers and / or foaming agents are, for example, nonionic and anionic emulsifiers, such as polyoxyethylene-fatty acid esters, polyoxyethylene-fatty alcohol ethers, such as alkylaryl glycol ethers, alkyl sulfones. Acids, alkylsulfates, arylsulfonic acids and albumin hydrolysates.

Suitable as dispersants are, for example, lignin-sulfite waste liquors and methylcellulose.

Adhesives such as carboxymethyl cellulose and natural and synthetic polymers in powder, granular or latex form such as gum arabic, polyvinyl alcohol, polyvinyl acetate and natural phospholipids such as cephalin and lecithin, and synthetic phospholipids are used. It can be used in formulations. Furthermore, mineral oils and vegetable oils can also be used as additives.

Colorants such as inorganic pigments such as iron oxide, titanium oxide and Prussian blue, and organic dyes,
For example, alizarin dyes, azo dyes and metal phthalocyanine dyes, and micronutrients such as iron, manganese, boron, copper, cobalt, molybdenum and zinc salts can be used.

The formulations are generally 0.1 to 95% by weight,
It preferably contains 0.5 to 90% by weight of active compound.

The substituted 2-arylpyrroles of the formula (I) according to the invention can be incorporated into other known active compounds in commercially available formulations, or in application forms prepared from these formulations which can be applied immediately or the like, For example, insecticides, attractants, fertility agents (ster)
ilants), acaricides, nematicides, fungicides, growth regulators, or mixtures with herbicides. As an insecticide,
Examples thereof include phosphoric acid ester, carbamate ester, carboxylic acid ester, chlorinated hydrocarbon, phenylurea, microorganism-producing substance and the like.

The 2-arylpyrroles of the formula (I) according to the invention can additionally be present in commercial formulations or in the application forms prepared from these formulations, as a mixture with synergists. Synergists do not need their activity per se,
A compound which increases the activity of the active compound by adding it.

The active compound concentrations in the application forms prepared from the commercial formulations can be varied within wide limits. The active compound concentrations in the application forms are from 0.000001 to 95.
%, Preferably 0.0001 to 1% by weight.

The compound is used in the usual manner suitable for the application form.

When the active compound is used against hygiene pests and stored product pests, it shows outstanding residual effects on wood and clay and on alkali on lime-treated substrates. Shows good stability.

The 2Y arylpyrroles of the formula (I) according to the invention are also suitable for controlling insects and mites in the field of livestock and livestock, for example increased milk production, increased weight of meat animals, more beautiful fur. And better results than hair production, livestock prolongation, etc. can be achieved by controlling these pests.

The 2-arylpyrroles of formula (I) of the present invention may be administered orally by methods known in the art, eg in the form of tablets, capsules, drinks, granules, eg by dipping, spraying or pouring. It can be applied dermally or externally, by spot application or dusting, powder dusting, and parenterally, for example in the form of injections, or it can also be used through the bait feed. Applications in the form of molded articles (eg, animal flea collars or ear tags for similar purposes) are also possible.

The invention is further described by the following examples.

[0119]

EXAMPLES Manufacturing Examples Example 1 (Method A)

[0120]

[Chemical 35]

1.9 g (6.1 mmol) of 2- (4-chlorophenyl) -5- (trifluoromethylsulfonyl) -pyrrole were dissolved in 50 ml of chloroform,
2.4 ml (47 mmol) of bromine are added to the same solution and the resulting mixture is stirred at room temperature for 10 hours. The solution is then evaporated in a rotary evaporator and the product obtained is codistilled twice with toluene.

Yield: 2.3 g (97% of theory) of 2-
(4-Chlorophenyl) -3-bromo-5- (trifluoromethylsulfonyl) -pyrrole is obtained.

See Table 1 for physical data.

Example 2 (Method B)

[0125]

[Chemical 36]

2.86 g (5.7 mmol) of 2- (3,
4-dichlorophenyl) -3,4-dibrolomo-5-
35 ml of (dichlorofluoromethylthio) -pyrrole
Is dissolved in chloroform and the resulting solution is cooled to -25 ° C. 3.6 g of m-chloroperbenzoic acid solution (concentration: 5
A solution of 5%) (11.5 mmol) in 50 ml of chloroform is added dropwise over 8 minutes. Continue stirring at room temperature for 5 hours. The reaction solution is then twice with 50 ml each of Na ₂ SO ₄ solution and 50% with Na ₂ CO ₃ 10% solution.
Wash twice with each ml. Drying the organic phase over Na ₂ SO ₄ ,
Evaporate in a rotary evaporator.

Yield: 2.5 g (87% of theory) of 2-
(3,4-dichlorophenyl) -3,4-dibrolomo-5
-(Dichlorofluoromethylsulfonyl) -pyrrole is obtained.

See Table 1 for physical data.

Example 3 (Method C)

[0130]

[Chemical 37]

3 g (6.6 mmol) of 2- (3,4-dichlorophenyl) -3,4-dibrolomomo-5- (dichlorofluoromethylsulfonyl) -pyrrole were dissolved in 80 ml of dry tetrahydrofuran and 0.8 g
Add (6.0 mmol) potassium tert.-butyrate to the resulting solution. 1.1 g (7.2 mmol) of ethyl N-methyl-N-chloromethyl-carbamate are dissolved in tetrahydrofuran and added dropwise to the mixture.
The resulting mixture is stirred at room temperature for 17 hours, then poured into water and extracted using dichloromethane. Extract is N
Dry over a ₂ SO ₄ , evaporate and chromatograph the residue on a silica gel column (eluent: petroleum ether / CH ₂ Cl ₂ = 1: 1).

Yield: 1.4 g (37% of theory) of 1-
(N-methyl-ethoxycarbonylamino-methyl)-
2- (3,4-dichlorophenyl) -3-bromo-5-
(Dichlorofluoromethylsulfonyl) -pyrrole is obtained.

See Table 1 for physical data.

Example 4 (Method D)

[0135]

[Chemical 38]

3.0 g (6.64 mmol) of 2- (4-
Chlorophenyl) -3,4-dibrolomo-5- (dichlorofluoromethylsulfonyl) -pyrrole was dissolved in 55 ml of dry tetrahydrofuran and 0.78 g
(6.9 mmol) potassium tert.-butyrate is added to the same solution. A solution of 0.69 g (7.3 mmol) of chloromethylethyl ether dissolved in about 20 ml of tetrahydrofuran was added dropwise, and the resulting mixture was stirred at room temperature for 19 hours.
Stir for hours. Then the mixture is poured into water, extracted with dichloromethane and the organic phase is washed twice with water. The organic phase is dried over MgSO _4, and evaporated.

Yield: 1 of 2.96 g (87% of theory)
-(Ethoxymethyl) -2- (4-chlorophenyl)-
3,4-Dibrolomo-5- (dichlorofluoromethylsulfonyl) -pyrrole is obtained.

See Table 1 for physical data.

The compounds of formula (I) listed in Table 1 below are also prepared by the method A of the present invention in the same manner as in Examples 1 to 4.
To the general information for Method E above.

[0140]

[Table 1]

[0141]

[Table 2]

[0142]

[Table 3]

[0143]

[Table 4]

[0144]

[Table 5]

[0145]

[Table 6]

[0146]

[Table 7]

[0147]

[Table 8]

[0148]

[Table 9]

[0149]

[Table 10]

[0150]

[Table 11]

[0151]

[Table 12]

[0152]

[Table 13]

[0153]

[Table 14]

[0154]

[Table 15]

[0155]

[Table 16]

[0156]

[Table 17]

[0157]

[Table 18]

[0158]

[Table 19]

[0159]

[Table 20]

[0160]

[Table 21]

[0161]

[Table 22]

[0162]

[Table 23]

[0163]

[Table 24]

[0164]

[Table 25]

[0165]

[Table 26]

[0166]

[Table 27]

[0167]

[Table 28]

[0168]

[Table 29]

[0169]

[Table 30]

Preparation of Precursor Example-1 10 g (0.057 mol) 2- (3-chlorophenyl) -phenyl were dissolved in 50 ml dry ether and 6.0 g (0.057 mol) Na ₂ CO ₃ Is added. The resulting mixture was cooled to -20 ° C and 6.6 ml
A solution of (0.0627 mol) chlorodifluoromethylsulfenyl chloride in 20 ml ether is slowly added dropwise. The mixture is stirred at the same temperature for 2.5 hours, the solid is filtered off and washed with ether. It washed filtrate with water, dried over MgSO _4, and evaporated.

The dark blue crude product is purified by filtration over silica gel (CH ₂ CH ₂ / petroleum ether = 1: 1).

Yield: 10.1 g (61% of theory), 2
-(3-Chlorophenyl) -phenyl-5- (chlorodifluoromethylthio) -pyrrole is obtained.

See Table 2 for physical data.

The precursors of formula (V) listed in Table 2 below can be prepared in the same manner.

[0175]

[Table 31]

[0176]

[Table 32]

Example II-1 4.5 g (13.2 mmol) of 2- (3-chlorophenyl) -phenyl-5- (dichlorofluoromethylthio)
-Pyrrole (V-5) is dissolved in 45 ml of methylene chloride and cooled to -10 ° C. 8.29g (26.4mmo
A solution of 1) of 55% strength m-chloroperbenzoic acid in 70 ml of chloroform is added over 1 hour and the mixture obtained is stirred at room temperature for 3 hours.

The reaction mixture was adjusted to 5 per Na ₂ SO ₄ solution.
Wash twice with 0 ml, dry over Na ₂ SO ₄ and evaporate.

Yield: 2.96 g (91% of theory) of 2-
(3-Chlorophenyl) -phenyl-5- (dichlorofluoromethylsulfonyl) -pyrrole is obtained.

See Table 3 for physical data.

Precursors of formula (II) listed in Table 3 below are similarly prepared.

[0182]

[Table 33]

[0183]

[Table 34]

[0184]

[Table 35]

Use Examples The compounds of the formula (A) from the prior art, shown below in the use examples below, were used as comparative substances.

[0186]

[Chemical Formula 39]

(The compound is a European patent (EP-A)
No. 0,347,488. See Example 9, page 27, line 42 of the same patent. ) In the active compounds according to the invention, the example numbers correspond to the production example numbers. Example A Plutella Test Solvent: 7 parts by weight of dimethylformamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether 1 part by weight of active compound in the above amounts to make a suitable formulation of active compound. Mixed with the solvent and the above amount of emulsifier,
The resulting stock solution was diluted with water to the desired concentration.

Cabbage (Brassica olera)
(cea) leaves are soaked in the active compound preparation of the desired concentration, while the leaves are still wet (Plutella ma
Culipennis) larvae were attached.

After a specific period, konaga larvae were exterminated (death).
The rate was measured in%. 100% means that all larvae have died, 0% indicates that no larvae have been killed.

In this test, compared with the prior art, the production examples (15), (19), (20), (21), (24),
(25), (26), (27), (29), (30), (4
The compound of 1) showed an excellent% activity.

After 7 days, at a concentration of 0.001% each,
The control rate of the comparative compound (A) was 20%, whereas the control rate of the compounds of the present invention was 100%.

[0192]

[Table 36]

[0193]

[Table 37]

[0194]

[Table 38]

Example B Nephotettix Test Solvent: 7 parts by weight of dimethylformamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether 1 part by weight of active compound in the above-mentioned amount to make a suitable formulation of active compound. Mixed with the solvent and the above amount of emulsifier,
The resulting stock solution was diluted with water to the desired concentration.

Seedlings of rice (Oryza sativa)
Soaked in the desired concentration of active compound formulation while the leaves were still wet (Nephotettix ci)
(ncticeps) larvae were attached.

After a certain period of time, the abactericidal rate was measured in%. 100% means that all leafhoppers have died and 0% indicates that no one was killed.

In this test, for example, the compound of Preparation Example (11) showed superior activity compared to the compounds of the prior art.

After 7 days, at a concentration of 0.01% each, the comparative compound (A) showed an extermination rate of 20%, whereas the active compound of the invention showed 100%.

[0200]

[Table 39]

Example C Tetranychus (OP resistant species) test Solvent: 7 parts by weight of dimethylformamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether 1 part by weight to make a suitable formulation of the active compound. The active compound is mixed with the above-mentioned amount of solvent and the above-mentioned amount of emulsifier,
The resulting stock solution was diluted with water to the desired concentration.

Greenhouse spider mite (Tet) at all stages of development
runnychus vulgaris) bean (Pha
(seolus vulgaris) seedlings were infested and the seedlings were dipped in the active compound formulation at the desired concentration.

After a specified period of time, the effect was measured in%.
100% means that all ticks have died, 0% means 1
It indicates that no one was killed.

In this test, manufacturing examples (18), (19), (20), (24), (2
The compounds 8), (30) and (41) showed excellent% activity. The comparative compounds had no effect, whereas the active compounds of the invention showed a eradication rate of 98 to 100% after 7 days at the respective concentrations of 0.1%.

[0205]

[Table 40]

[0206]

[Table 41]

Example D Flies Test Animal tested: Musca domestic (Musca domestic)
a, WHO (N) system) Solvent: 35 parts by weight of ethylene glycol monomethyl ether Emulsifier: 35 parts by weight of nonylphenol polyglycol ether To prepare a suitable formulation, 3 parts by weight of the active compound in 7 parts by weight of It was mixed with the above solvent / emulsifier mixture and the resulting emulsion stock solution was diluted with water to the desired specific concentration.

2 ml of this active compound preparation was pipetted and poured into a disc-shaped filter paper (diameter 9.5 cmφ) placed in a watch glass of an appropriate size. 25 after the filter paper dries
The test flies were transferred into a watch glass and covered.

After 6 hours, the effect of the active compound preparation is determined. The effect is expressed in%. 100% means that all the flies have died, 0% means that none have died.

In this test, manufacturing examples (3), (1
9), (20), (26), (27), (28), (3
The compounds 0), (41), (42) showed superior activity compared to the prior art compounds.

At a typical concentration of 1000 ppm, comparative compound (A) had no effect. On the contrary, the effect of the above-mentioned active compounds of the present invention was 50% or more, and in some cases even 100%.

[0212]

[Table 42]

[0213]

[Table 43]

[0214]

[Table 44]

Example E Drosophila, flesh fly larva test Test animal: Lucilia cuprin
Larvae of a) Solvent: 35 parts by weight of ethylene glycol monomethyl ether Emulsifier: 35 parts by weight of nonylphenol polyglycol ether 3 parts by weight of active compound are mixed with 7 parts by weight of the above mixture to prepare a suitable formulation. The emulsified stock solution thus obtained was diluted with water to a desired specific concentration.

About 20 fruit flies (Lucilia c)
uprina res. ) Larva is about 1 cm in it
Placed in a test tube containing ³ horse meat and 0.5 ml of active compound formulation.

After 24 hours, the extermination rate is measured. 100%
Means that all fly larvae have died, 0% indicates that no larvae have died.

In this test, as compared with the compounds of the prior art, Preparation Examples (9), (19), (20), (2
The compounds of 6), (27), (28) and (30) are
It showed excellent activity.

At a typical concentration of 1000 ppm, the active compounds according to the invention each showed 100% control, whereas the comparative compound (A) had no effect.

[0220]

[Table 45]

[0221]

[Table 46]

Example F Cockroach Test Test Animal: German cockroach (Blattella g)
ermanica) or American cockroach (Perip)
laneta americana) Solvent: 35 parts by weight of ethylene glycol monomethyl ether Emulsifier: 35 parts by weight of nonylphenol polyglycol ether 3 parts by weight of active compound 7 parts by weight of the above solvent / emulsifier mixture to prepare a suitable formulation. The resulting emulsified stock solution was diluted with water to the desired specific concentration.

2 ml of this active compound preparation was pipetted and poured into a disc-shaped filter paper (diameter 9.5 cmφ) placed in a watch glass of an appropriate size. After the filter paper has dried, 5 test animals [B. germanic (B. germanic)
a) or American cockroach (P. americanan)
a)] was transferred into a watch glass and covered.

After 3 days, the effect of the active compound formulation is determined. The effect is expressed in%. 100% means that all cockroaches died, 0% indicates that no one was dead.

In this test, for example, the compound of Preparation Example (30) showed superior activity compared to the prior art compounds.

At a typical concentration of 1000 ppm, the active compounds according to the invention showed 100% control,
Even if the concentration of the comparative compound (A) is 1,000 ppm, it is about 5
It was only 0%.

[0227]

[Table 47]

The main features and aspects of the present invention are as follows.

1. General formula (I)

[0230]

[Chemical 40]

In the formula, R ¹ and R ² independently represent hydrogen or halogen. However, at least one of the two radicals R ¹ or R ² represents halogen, R ³ represents hydrogen, halogen or optionally substituted alkyl, Wherein R ⁵ represents hydrogen or optionally substituted alkyl and R ⁶ is hydrogen, optionally substituted alkyl or group Wherein R ⁷ and R ⁸ independently of one another represent hydrogen, alkyl, alkenyl, alkynyl, alkoxycarbonyl, alkenoxycarbonyl, alkynoxycarbonyl or acyl, and also R ⁷ and R ⁸ are bound to them. It is also possible for it to form a ring with an N atom which is present, Ar represents an optionally substituted aryl, X
¹ and X ² each independently represent hydrogen or halogen,
And substituted 2-arylpyrroles, wherein n represents 0, 1 or 2.

2. In the general formula (I) described in the above item ¹ , R ¹ and R ² independently represent hydrogen, bromine, or chlorine, and at least one of the groups R ^{1 and} R ² represents bromine or chlorine; ³ is hydrogen, fluorine, chlorine, bromine,
Or (optionally substituted by 1 to 5 fluorine, chlorine or bromine atoms, identical or different substituents) C ₁ -C ₅ -alkyl, Wherein R ⁵ is hydrogen, or (optionally by 1 to 5 identical or different halogen atoms, C ₁ -C ₅ -alkoxy, C ₁ -C ₅ -alkylthio, C ₁ -C ₅ -acyloxy, C ₂ — C _6- Alkoxycarbonyl, phenyl, cyano, or nitro) C _1-
Represents C ₅ -alkyl and R ⁶ is hydrogen or (optionally by 1 to 5 identical or different halogen atoms, C ₁ -C ₈ -alkoxy, C ₁ -C ₈ -alkylthio,
C ₁ -C ₆ -acyloxy, C ₂ -C ₈ -alkoxycarbonyl, phenyl, cyano or nitro may be substituted) C ₁ -C ₆ -alkyl or R ⁶ is Wherein R ⁷ and R ⁸ independently of one another are hydrogen, C ₁ -C ₈ -alkyl, C ₃ -C ₈ -alkenyl, or C ₃ -C ₈ -alkynyl (wherein the alkyl, alkenyl and alkynyl are each optionally 1 to 6 identical or different halogen atoms, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -alkylthio, C ₁ -C ₆ -acyloxy, (C ₁ -C ₆ -alkoxy) -carbonyl, optionally substituted Optionally substituted by phenyl, cyano, or nitro), or (C ₁ -C ₈ -alkoxy) -carbonyl,
(C ₃ -C ₈ -Alkenoxy) carbonyl, or (C ₃
—C ₈ -Alquinoxy) -carbonyl, (the same alkoxy, alkenoxy and alkynoxy are each optionally 1 to 6 identical or different halogen atoms, C ₁ —
C ₆ - alkoxy, C ₁ -C ₆ - alkylthio, C ₁ -C ₆
-Acyloxy, (C ₁ -C ₆ -alkoxy) -carbonyl, optionally substituted by phenyl, cyano, or nitro), or C ₁
-C ₈ -acyl (wherein the acyl is optionally ₁ to 6 identical or different halogen atoms, C ₁ -C ₆ -alkoxy, C ₁
-C ₆ -alkylthio, C ₁ -C ₆ -acyloxy, (C ₁
--C ₆ -alkoxy) -carbonyl, optionally substituted phenyl, cyano, or nitro)) or R ⁷ and R ⁸ are the same as the N atom to which they are attached. Together, they form a 4- to 8-membered ring, Ar optionally being halogen, C ₁ -C ₈
- alkyl, C ₂ -C ₈ - alkenyl or C ₂ -C _8, -
Alkynyl (wherein alkyl, alkenyl and alkynyl are each optionally ₁ to 6 identical or different halogen atoms, C ₁ -C ₅ -alkoxy, C ₁ -C ₅ -alkylthio, C ₁ -C ₅ -acyloxy, and alkoxy) ,
The alkylthio groups may each be substituted by 1 to 6 halogen atoms) C ₁ -C ₈ -alkoxy, C ₂ -C ₈ -alkenoxy or C ₂ -C ₈ -alkynoxy (the same alkoxy, alkenoxy and alkynoxy). Are each optionally substituted by 1 to 6 identical or different halogen atoms) C ₁ -C ₈
- alkylthio, C ₂ -C ₈ - alkenylthio or C,
_2- C ₈ -alkynylthio (the same alkylthio, alkenylthio and alkynylthio are each optionally 1 to 6
C ₂ -C ₈ -acyloxy (wherein the acyloxy may be optionally substituted by 1 to 6 halogen atoms), amino (wherein the amino is optionally 1 to 6) From two identical or different 1 to 8 carbon atoms and, if appropriate, an alkyl group having 1 to 6 halogen atoms, or a halogenoalkyl group), nitro or cyano Represents a phenyl, which may be mono- or pentasubstituted by the same or different substituents from the group consisting of, wherein X ¹ and X ² independently of one another represent hydrogen, fluorine, chlorine or bromine, and n is A 2-arylpyrrole representing 0, 1, or 2.

3. R in the general formula (I) described in the first item
¹ and R ² each independently represent hydrogen, bromine, or chlorine, at least one of the groups R ¹ or R ² represents bromine or chlorine, and R ³ represents hydrogen, fluorine, chlorine, bromine, or (optionally 1 to 5 C ₁ -C ₄ -alkyl, which may be substituted by the same or different substituents selected from the group consisting of fluorine, chlorine or bromine atoms. Wherein R ⁵ is hydrogen, or (optionally by 1 to 5 identical or different halogen atoms, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -alkylthio, C ₁ -C ₄ -acyloxy, C ₂ — C ₅ -Alkoxycarbonyl, optionally substituted by phenyl, cyano, or nitro) C ₁ -C
Represents ₄ -alkyl, and R ⁶ is hydrogen, or (optionally 1
To 5 identical or different halogen atoms, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -alkylthio,
C ₁ -C ₅ -acyloxy, C ₂ -C ₆ -alkoxycarbonyl, phenyl, cyano, or nitro) C ₁ -C ₅ -alkyl, or Wherein R ⁷ and R ⁸ are independently of each other hydrogen, C ₁ -C ₆ -alkyl, C ₃ -C ₆ -alkenyl, or C ₃ -C ₆ -alkynyl (wherein the alkyl, alkenyl and alkynyl are each independently 1 to 5 identical or different fluorine and / or chlorine atoms, C ₁ -C ₄ -alkoxy, C ₁
-C ₄ - alkylthio, C ₁ -C ₄ - acyloxy, (C ₁
-C ₄ -alkoxy) -carbonyl, optionally substituted phenyl, cyano, or optionally substituted by nitro), or (C ₁ -C ₆ -alkoxy) -carbonyl, (C ₃ -C _6- Alkenoxy) carbonyl, or (C ₃ -C ₆ -alkynoxy) -carbonyl, (the same alkoxy, alkenoxy and alkynoxy are each optionally 1 to 5 identical or different fluorine and / or chlorine atoms, C ₁ -C ₄ -alkoxy,
C ₁ -C ₄ -alkylthio, C ₁ -C ₄ -acyloxy,
Represents (C ₁ -C ₄ -alkoxy) -carbonyl, optionally substituted by phenyl, cyano, or nitro) or C ₁ -C ₆ -acyl (wherein the acyl is optionally from 1 to 5) Identical or different fluorine and / or chlorine atoms, C ₁ -C ₄ -alkoxy, C _1-
C ₄ - alkylthio, C ₁ -C ₄ - acyloxy, (C ₁ -
C ₄ -alkoxy) -carbonyl, optionally substituted phenyl, cyano, or nitro) or R ⁷ and R ⁸ together with the N atom to which they are attached. To form a 4- to 8-membered ring, and Ar is optionally fluorine, chlorine, or bromine,
C ₁ -C ₆ - alkyl, C ₂ -C ₆ - alkenyl or C,
_2- C ₆ -alkynyl (wherein alkyl, alkenyl and alkynyl are each independently 1 or 5 fluorines and /
Or a chlorine atom, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -alkylthio, C ₁ -C ₄ -acyloxy, and here the alkoxy and alkylthio groups each have 1 to 5 fluorine and / or chlorine atoms. C ₁ -C ₆ -alkoxy, C ₂ -C ₆ -alkenoxy, or C ₂ -C ₆ -alkynoxy (the same alkoxy,
Alkenoxy and alkynoxy may each optionally be substituted by 1 to 5 fluorine and / or chlorine atoms) C ₁ -C ₆ -alkylthio, C ₂ -C _6-
Alkenylthio or C ₂ -C _6, - alkynylthio (the alkylthio, each alkenylthio and alkynylthio, may be substituted to 1 at any time by the 5 fluorine and / or chlorine atoms), C ₂ -C ₆ - Acyloxy (wherein the acyloxy may be optionally substituted by 1 to 5 halogen atoms), amino (wherein the amino is optionally 1 to 2 identical or different 1 to 6 carbon atoms and, if appropriate, Phenyl optionally mono- or tetra-substituted by the same or different substituents from the group consisting of alkyl groups having one or more fluorine and / or chlorine atoms), nitro or cyano. represents and represents hydrogen, fluorine or chlorine independently wherein X ¹ and X ² each other, their Te n represents a 0, 1, or 2, 2-
Arylpyrrole.

4. General formula (I)

[0235]

[Chemical 41]

In the formula, R ¹ and R ² independently represent hydrogen or halogen. However, at least one of the two radicals R ¹ or R ² represents halogen, R ³ represents hydrogen, halogen or optionally substituted alkyl, Wherein R ⁵ represents hydrogen, or optionally substituted alkyl, and R ⁶ is hydrogen, optionally substituted alkyl or Wherein R ⁷ and R ⁸ independently of one another represent hydrogen, alkyl, alkenyl, alkynyl, alkoxycarbonyl, alkenoxycarbonyl, alkynoxycarbonyl or acyl, and R ⁷ and R ⁸ are bound to them. It is also possible to form a ring with N atom, A
r represents optionally substituted aryl, X ¹ and X ² independently of each other represent hydrogen or halogen, and n represents 0, 1 or 2, in the process for the preparation of substituted 2-arylpyrroles, (A / B) A) Formula (II)

[0237]

[Chemical 42]

A 2-arylpyrrole of the formula where R ³ , X ¹ , X ² and Ar have the meanings given above and n is 1 or 2 (Method A) Or B) Formula (III)

[0239]

[Chemical 43]

Wherein R ¹ , R ² , R ³ , X ¹ , X ² and Ar
Has the meanings given above, the 2-arylpyrrole of is reacted with an oxidizing agent (method B) to give a compound of formula (Ia)

[0241]

[Chemical 44]

Wherein R ¹ , R ² , R ³ , X ¹ , X ² or Ar
Has the meanings given above and n is 1 or 2 to obtain a 2-arylpyrrole of or C) of the general formula (Ia), in which R ¹ , R ² , R ³ , X ¹ ,
X ² and Ar have the meanings given above and n is 1
2-arylpyrroles of formula (IV)

[0243]

Embedded image R ⁹ —X ³ (IV) Wherein R ⁵ and R ⁶ have the meanings given above, and X ³ represents an anion residual group,
If appropriate, the reaction is carried out in the presence of a base and / or, if appropriate, in the presence of a diluent, of formula (Ib)

[0244]

[Chemical formula 46]

A 2-arylpyrrole is obtained in which R ¹ , R ² , R ³ , R ⁹ , X ¹ , X ² and Ar have the meanings given above and n is 1 or 2. Method C) or D) of the general formula (III), wherein R ¹ , R ² , R ³ ,
X ¹ , X ² and Ar are 2-arylpyrroles of the formula (IV) having the meanings given above.

[0246]

Embedded image R ⁹ —X ³ (IV) Wherein R ⁵ and R ⁶ have the meanings given above, and X ³ represents an anion residual group,
If appropriate, the reaction is carried out in the presence of a base and / or, if appropriate, in the presence of a diluent, of formula (Ic)

[0247]

[Chemical 48]

A 2-arylpyrrole is obtained in which R ¹ , R ² , R ³ , R ⁹ , X ¹ , X ² and Ar have the meanings given above and n is 1 or 2 ( Method D) or E) Formula (V)

[0249]

[Chemical 49]

2-arylpyrroles of the formula R ³ , X ¹ , X ² and Ar have the meanings given above are reacted with a halogenating agent to give a compound of formula (Id)

[0251]

[Chemical 50]

Wherein R ¹ , R ² , R ³ , X ¹ , X ² and Ar
Has the meaning given above, and n is 0, 2-
A production method comprising obtaining an arylpyrrole (method E).

5. Formula (I) described in the above first to third terms
A pest control agent comprising at least one of the substituted 2-arylpyrroles of

6. Formula (I) described in the above first to third terms
Use of substituted 2-arylpyrroles for controlling pests.

7. Formula (I) described in the above first to third terms
A method for controlling pests, which comprises causing the substituted 2-arylpyrrole of 1. to act on a pest and / or its environment. 8. A method for producing a pest control agent, which comprises mixing the substituted 2-arylpyrrole of the formula (I) described in the above 1 to 3 with a spreading agent and / or a surfactant.

9. General formula (II)

[0257]

[Chemical 51]

Wherein n represents 1 or 2, Ar represents optionally substituted aryl, R ³ represents hydrogen, halogen, or optionally substituted alkyl, and X ¹ and X ² are Substituted 2-arylpyrroles, which, independently of one another, represent hydrogen or halogen.

10. Formula (V)

[0260]

[Chemical 52]

Substituted 2-arylpyrroles, wherein Ar, R ³ , X ¹ and X ² have the meaning given in section 9.

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Albrecht Malhort Germany Day 51373 Lech Elksen Karl-Dowisberg-Schut Larce 329 (72) Inventor Schutte Juan Behm Germany Day 51065 Cologne Andreas Griffy Ussyutrase 9 (72) Inventor Christoph Erderen Germany Day 42799 Reichlingen Unterbiyuscher Hof 22 (72) Inventor Ulrike Bahendorf-Neumann Germany Day 40789 Monheim Crissia Schutlerse 81 (72) Inventor Birhelm Schyutendel Germany Day 42113 Butspertal Inden Birken 55

Claims (7)

[Claims] 1. A compound represented by the general formula (I): In the formula, R ¹ and R ² independently represent hydrogen or halogen. However, at least one of the two radicals R ¹ or R ² represents halogen, R ³ represents hydrogen, halogen or optionally substituted alkyl, Wherein R ⁵ represents hydrogen, or optionally substituted alkyl, and R ⁶ is hydrogen, optionally substituted alkyl or Wherein R ⁷ and R ⁸ independently of one another represent hydrogen, alkyl, alkenyl, alkynyl, alkoxycarbonyl, alkenoxycarbonyl, alkynoxycarbonyl or acyl, and also R ⁷ and R ⁸ are bound to them. It is also possible for it to form a ring with an N atom which is present, Ar represents an optionally substituted aryl, X
¹ and X ² each independently represent hydrogen or halogen,
And substituted 2-arylpyrroles, wherein n represents 0, 1 or 2. 2. A compound represented by the general formula (I): In the formula, R ¹ and R ² independently represent hydrogen or halogen. However, at least one of the two radicals R ¹ or R ² represents halogen, R ³ represents hydrogen, halogen or optionally substituted alkyl, Wherein R ⁵ represents hydrogen, or optionally substituted alkyl, and R ⁶ is hydrogen, optionally substituted alkyl or Wherein R ⁷ and R ⁸ independently of one another represent hydrogen, alkyl, alkenyl, alkynyl, alkoxycarbonyl, alkenoxycarbonyl, alkynoxycarbonyl or acyl, and R ⁷ and R ⁸ are bound to them. It is also possible to form a ring with N atom, Ar
Represents an optionally substituted aryl, X ¹ and X ² each independently represent hydrogen or halogen, and n represents 0, 1 or 2, A / B) A) Formula (II) A ^2- arylpyrrole of the formula where R ³ , X ¹ , X ² and Ar have the meanings given above and n is 1 or 2 (Method A), or B) Formula (III): A 2-arylpyrrole of the formula wherein R ¹ , R ² , R ³ , X ¹ , X ² and Ar have the meanings given above are reacted with an oxidant (method B) to give a compound of formula (Ia) 5] A 2-arylpyrrole of the formula R ¹ , R ² , R ³ , X ¹ , X ² or Ar has the meanings given above and n is 1 or 2, or C) 2-arylpyrroles of formula (IV) of Ia), in which R ¹ , R ² , R ³ , X ¹ , X ² and Ar have the meanings given above and n is 1 or 2. Embedded image R ⁹ —X ³ (IV) And X ³ represents an anion residual group, is reacted, if appropriate, in the presence of a base and / or, if appropriate, a diluent, to give a compound of formula (Ib) Chemical 7] 2-wherein R ¹ , R ² , R ³ , R ⁹ , X ¹ , X ² and Ar have the meanings given above and n is 1 or 2.
Arylpyrrole is obtained (method C), or D) of the general formula (III), in which R ¹ , R ² , R ³ ,
X ¹ , X ² and Ar have the meanings given above and a 2-arylpyrrole is represented by the formula (IV) R ⁹ -X ³ (IV) And X ³ represents an anion residual group, is reacted, if appropriate, in the presence of a base and / or, if appropriate, a diluent, to give a compound of formula (Ic) Chemical 9] 2-wherein R ¹ , R ² , R ³ , R ⁹ , X ¹ , X ² and Ar have the meanings given above and n is 1 or 2.
Arylpyrrole is obtained (Method D) or E) Formula (V) A ^2- arylpyrrole of the formula, wherein R ³ , X ¹ , X ² and Ar have the meanings given above, are reacted with a halogenating agent to give a compound of formula (Id) Wherein R ¹ , R ² , R ³ , X ¹ , X ² and Ar have the meanings given above and n is 0 (process E). Manufacturing method. 3. A pest control agent comprising at least one substituted 2-arylpyrrole of the formula (I) according to claim 1 or 2. 4. A method for controlling pests, which comprises acting the substituted 2-arylpyrrole of the formula (I) according to claim 1 or 2 on a pest and / or its environment. 5. A method for producing a pest control agent, which comprises mixing the substituted 2-arylpyrrole of the formula (I) according to claim 1 or 2 with a spreading agent and / or a surfactant. 6. A compound represented by the general formula (II): Wherein n represents 1 or 2, Ar represents optionally substituted aryl, R ³ represents hydrogen, halogen, or optionally substituted alkyl, and X ¹ and X ² independently of one another. A substituted 2-arylpyrrole, which represents hydrogen, halogen or halogen. 7. Formula (V): Substituted 2-arylpyrroles, wherein Ar, R ³ , X ¹ and X ² have the meanings given in claim 6.